Synthesis of 2-hydroxy-3-methylbut-3-enyl substituted coumarins and xanthones as natural products. Application of the Schenck ene reaction of singlet oxygen with ortho-prenylphenol precursors

Application of our original photooxidation–reduction methodology to prenylated dihydroxycoumarin and trihydroxyxanthone compounds led to the corresponding ortho-(2-hydroxy-3-methylbut-3-enyl)phenol derivatives with yields ranging from 8 to 65%. In most of the reported experiments, the oxidation prod...

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Bibliographic Details
Published in:Tetrahedron 2004-03, Vol.60 (10), p.2293-2300
Main Authors: Helesbeux, Jean-Jacques, Duval, Olivier, Dartiguelongue, Caroline, Séraphin, Denis, Oger, Jean-Michel, Richomme, Pascal
Format: Article
Language:English
Subjects:
Coumarin
ortho-(2-Hydroxy-3-methylbut-3-enyl)phenols
Photooxygenation
Regioselectivity
Schenck ene reaction
Xanthone
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Summary:Application of our original photooxidation–reduction methodology to prenylated dihydroxycoumarin and trihydroxyxanthone compounds led to the corresponding ortho-(2-hydroxy-3-methylbut-3-enyl)phenol derivatives with yields ranging from 8 to 65%. In most of the reported experiments, the oxidation products distribution, after the photooxygenation step, was controlled by the competition between the large group effect and the stabilising phenolic assistance effect. We also showed that ortho-(3-hydroxy-3-methylbut-1-enyl)phenol derivatives could be considered as biogenetic precursors of 2,2-dimethylbenzopyranic structures. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.01.033